20 Iconic Brad Pitt Style Moments and the Secret to His Infinite Appeal

Brad Pitt is a style chameleon who’s had a million different looks (and a zillion hairstyles) over the years. But it’s his inimitable, unshakeable, ever-lasting Brad Pitt-ness that makes him humanity’s favorite actor.

Brad Pitt—legendary actor, GQ Style cover star, Best Picture-winning producer, father, aspiring sculptor—is a very handsome man. This is a fact. Throughout his 30-odd years of public life, Pitt’s now iconic mug has inspired the kind of fandom that transcends age, gender, sexuality, race, class, and political party. As we’ve been saying around the office, Brad Pitt is like America's national parks: He unites us all.

Age 25, in 1988.

Michael Ochs Archives/Getty Images

Fight Club

20th Century Fox/Everett Collection

Check out his IMDB page, this guy's got range—and something for everyone. My favorite Brad Pitt movie is Meet Joe Black. He plays a sexy Angel of Death (yes) who just wants to know what it means to be human. This movie has everything: romance, magical realism, Anthony Hopkins, a steamy sex scene, Pitt’s picture-perfect frosted tips. It’s 3 hours and 1 minute of Pitt’s angelic face awash in a mask of naiveté as he learns, inevitably, to love. Just thinking about it gives me teenaged feels—it’s the epitome of a 90’s movie. It’s also the epitome of a Brad Pitt movie. Because what every Brad Pitt movie has in common is the enduring appeal of Brad Pitt.

With Anthony Hopkins in Meet Joe Black

Universal/Everett Collection

And he ain’t just for the girls and the gays. The year after Pitt appeared in Meet Joe Black, he became a cult legend as Tyler Durden in Fight Club. Every boyfriend I’ve ever had has ranked this movie in their top 10. A few have put it in their top 1. It’s the original Netflix and Chill pick—who among us has something better to do than watch Brad Pitt smoke cigarettes and fight? (Actually, I viscerally dislike this movie, but not even I can deny whatever combination of sinew and muscle Pitt is using to hypnotize us all.) Tyler Durden is the opposite of Joe Black—all-knowing, slick, kind of an asshole. His affair with Helena Bonham Carter’s twisted Marla, his “friendship” with Ed Norton, his ability to take a punch: that’s the kind of guy that men want to be. (Also, 12-pack abs.) One year later, Pitt’s in Snatch; a year after that, Ocean’s 11; the list, as they say, goes on and on. He’s someone for everyone.

1988

1992

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1993

Ron Galella/Getty Images

1994

SGranitz/Getty Images

1995

Ron Galella/Getty Images

1997

Rose Hartman/Getty Images

1989

Barry King/Getty Images

1991

Ron Galella/Getty Images

1992

2004

2005

2010

2011

2012

2016

Brad Pitt’s prolific career is a testament to his prolific ability to convincingly transform from sociopathic alter-ego to inscrutable hustler, to dashing thief all while maintaining a healthy level of raw, universal sex-appeal. But, I think the best part about Brad Pitt is that he’s not constantly reinventing himself. His characters are different, yes. His hair might change, his goatee might grow, his tips might frost—and yet he’s still the same reliably good looking, surprisingly relatable, deeply emo icon who at 53-years-old could probably approach me, you, your grandma, and your dog and melt us all.

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